California E&S Insurance

Doesn't seem much mention here of the note that this is CAD, so this is more like $7.5m. Not saying this is isn't fat, but if he is in an HCOL jurisdiction like vancouver or toronto, once you account for additional housing, then whether that is enough to feel becomes pretty sensitive to spend profile. Capital gains works a little differently in Canada but I think sub $250k CAD the rate will be around 25% (higher rate, but 1/3rd of the gains are tax free). Point is, it's tons of money, but I get why OP could easily say "this doesn't feel like enough" relative to sitting on ~$15m US before this all went down.

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